Our Under-18s were eliminated in the Fourth Round of this season's FA Youth Cup after a 1-0 defeat against Portsmouth at White Hart Lane.
Despite dominating for large periods of the match, Alex Inglethorpe's side could not find a way past the dogged and determined visitors in front of over a thousand fans.
Instead we were undone by a sucker punch from Nadir Ciftci just after the hour mark that ended our cup dreams for another season.
Much credit, however, must go to Pompey goalkeeper Liam O'Brien, who produced a match-winning performance as it became one-way traffic towards his goal as the game progressed.
But we looked the better side from the first whistle, with pacy right-winger Ryan Fredericks looking lively down the Spurs right-hand side and giving his full-back a torrid time throughout.
After quarter of an hour, a mazy solo run that became commonplace during the half ended with a shot to the near post that O'Brien blocked.
On 24 minutes, Fredericks again beat his man and pulled back for Dean Parrett who should have done better from 12 yards.
But the first 45 minutes was a far more even half, and arguably the best chances of the first half actually fell to the visitors.
Ellis Martin fired a good chance over the bar on 23 minutes after Gael Nlundulu's cross to the back post.
On 36 minutes, defender Steven Caulker misjudged a header and the industrious Ciftci latched onto the loose ball before firing over from inside the box - a real let off.
And we also had goalkeeper Jamie Butler to thank for stopping us falling behind with a first-class save from Nlundulu, who shot from a tight angle having been released by Ciftci.
At the other end, Paul-Jose M'Poku twice tested O'Brien; once with a rasping drive and again from inside the box on the stretch from Parrett's throughball.
It also took some good defending from Sam Nagri to deny Parrett after Tom Carroll's low ball five minutes before the break as we pushed forward towards the end of the half.
We carried this momentum into the second period, with Fredericks again looking threatening having beaten his marker in the box and forcing a near post block from O'Brien five minutes after the break.
The impressive goalkeeper then did well again to tip a downward header from Caulker over the bar from the resulting corner.
At this stage, Spurs were in the ascendancy - so the opening goal came as a bitter blow just after the hour mark.
The lively Ciftci picked up the ball up in a seemingly harmless position wide on the left, but then suddenly showed quick feet to step inside of right-back Jesse Waller-Lassen and curl a right foot shot over Butler into the far top corner.
What was most frustrating was that our best period of the game then followed without producing any reward.
Fredericks continued to provide the threat but Pompey's defending was resolute, backed up by a splendid performance from O'Brien.
On 72 minutes, he pulled off his best save of the match when a Harry Kane cross from the right was cleared only as far as left-back Carroll, whose powerful strike from the edge of the box was acrobatically tipped over.
However, there would have been little O'Brien could have done had Parrett got his low curling shot on target from the edge of the box having danced past a couple of challenges moments later.
Unfortunately, it whistled inches past the post as did yet another Fredericks effort on 77 minutes when Pompey left-back Billy Tsovolos was once again beaten all ends up inside the box.
O'Brien was back in action two minutes later when Kane climbed to meet Carroll's cross but saw his looping header plucked away from the top corner, but we were coming closer and closer.
Peter Gregory miskicked a long ball nine minutes from time, and substitute Kudus Oyenuga picked it up and curled a shot agonisingly wide from the edge of the box.
Parrett's inch-perfect delivery from free-kicks produced a further two late openings, with defender Nathan Byrne and Oyenuga both unable to convert.
So, somehow, Pompey managed to hold out for what was an unlikely victory for them, with our lads left to focus on the Premier Academy League for another season.
Spurs (4-1-4-1): Butler; Waller-Lassen, Caulker, Byrne, Carroll; Nicholson; Fredericks (McBride, 90), Parrett, Bostock, M'Poku (Oyenuga, 61); Kane
Subs not used: Archer, Durojaiye, Francis-Angol
Pompey (4-4-2): O'Brien; Gregory, Ryan, Nagri, Tsovolos (Seeley, 82); Nlundulu (Smith, 78), Goddard, Cuvelier, Martin; Ciftci, Walshe (Navas, 57)
Subs not used: Stockford, Jennings